Argentum iodatum

Base Information

• Chemical Name: Argentum iodatum
• CAS No.: 7783-96-2
• Molecular Formula: AgI
• Molecular Weight: 234.77
• UNII: 81M6Z3D1XE
• Nikkaji Number: J43.607K
• Mol file: 7783-96-2.mol

Synonyms:Silver(I)iodide;ARGENTUM IODATUM;SILVER IODIDE [MI];SILVER IODIDE [HSDB];ARGENTUM IODATUM [HPUS];AKOS015918228;SY009455

Chemical Property of Argentum iodatum

Chemical Property:

• Appearance/Colour: Yellow crystalline powder
• Melting Point: 557 °C
• Boiling Point: 1506 °C
• PSA: 0.00000
• Density: 5.68 g/mL at 25 °C(lit.)
• LogP: 0.88570
• Water Solubility.: 0.03 mg/L
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 233.80956
• Heavy Atom Count: 2
• Complexity: 0

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Safety Statements: S22:; S24/25:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: [Ag+].[I-]
• General Description: Silver iodide (AgI) serves as an effective mediator in the amination of allylic chlorides with lithium bis(trimethylsilyl)amide, enabling the synthesis of N,N-disilylallylamines with high regio- and stereoselectivity. It enhances reaction efficiency, particularly for alkyl-substituted substrates at sub-stoichiometric amounts, while phenyl-substituted variants require full equivalence. The active species are proposed to be lithium amide argentates, which modulate nucleophilicity and basicity, preserving sensitive functional groups. This method provides a selective and efficient route to valuable allylamine derivatives.

Refernces

Silver iodide mediated amination reaction of allylic chlorides with lithium bis(trimethylsilyl)amide: A new synthetic method of N,N- disilylallylamines via lithium amide argentates

10.1021/jo00078a024

The research investigates the nucleophilic substitution reaction of allylic chlorides with lithium bis(trimethylsilyl)amide (1) in the presence of silver iodide (AgI) to synthesize N,N-disilylallylamines. The purpose is to develop a new synthetic method for these compounds, which are important in organic synthesis. The study finds that AgI significantly enhances the reaction efficiency, with 0.1 or 0.5 equivalents of AgI being effective for alkyl-substituted allylic chlorides, while a stoichiometric amount is necessary for phenyl-substituted ones. The reaction proceeds with high regio- and stereoselectivity, preserving functional groups like oxygen-containing groups and chlorine. The researchers propose that lithium amide argentates, such as (Me3Si)2NAg(I)Li (20) and [(Me3Si)2N]2Ag(I)Li2 (21), form in the reaction mixture, controlling the nucleophilicity and basicity of 1. This is supported by 13C NMR studies. The conclusion is that AgI-mediated reactions offer a highly efficient and selective route to N,N-disilylallylamines, with the active species likely being lithium amide argentates.

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